Winchendon Holidays

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to £335 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Your Winchendon Holiday

When you choose a Winchendon holiday package, it's all about enjoying your adventure to the fullest. Delve into the highlights of this unique city knowing that all your travel needs have been worked out in advance. If seeing the sights is on your list of things to do during your trip to Winchendon, head over to popular attractions like Lake Dennison State Recreation Area. Your dream Winchendon holiday is just clicks away. Browse flights, hotels and more on Expedia for a getaway that's tailored to suit your style.

Winchendon Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Worcester Regional Airport (ORH)
Population
4,200
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Doanes Falls, Royalston Falls and Dunn State Park

Our pick of the best Winchendon Hotel Deals

Modern Waterfront Gem w/ Dock on Lake Monomonac
Modern Waterfront Gem w/ Dock on Lake Monomonac
Winchendon, Massachusetts
Stay at this holiday home in Winchendon. Enjoy an in-room coffee maker and air conditioning. Popular attractions Paradise Island and Blueberry Island are located ...
10/10 Exceptional! (4 reviews)
The Perfect Getaway
"We stayed here as our base for a week of college tours. Boy, was this the perfect place to come home to each evening to reset. We actually never ate out for dinner, because we wanted to eat in the home and watch the sunset over the lake. Also, waking up to enjoy breakfast and coffee, while listening ..."

Reviewed on 21 Apr 2025

Modern Waterfront Gem w/ Dock on Lake Monomonac
Modern Waterfront Gem w/ Dock on Lake Monomonac
Modern Waterfront Gem w/ Dock on Lake Monomonac
3 out of 5
Winchendon
Stay at this 3-star cottage in Winchendon. Enjoy free parking and air conditioning. Popular attractions Paradise Island and Blueberry Island are located ...
Modern Waterfront Gem w/ Dock on Lake Monomonac
The Colonial Hotel
The Colonial Hotel
3 out of 5
625 Betty Spring Road, Gardner, MA
Stay at this 3-star business-friendly hotel in Gardner. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the restaurant and the helpful ...
8.6/10 Excellent! (1,002 reviews)
"A truly grand New England hotel in every aspect. Super friendly and helpful staff."

Reviewed on 26 Jun 2025

The Colonial Hotel
See all 191 properties in Winchendon
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Winchendon travel package cost?
Starting from as low as , you can tailor your Winchendon package the way you want. Simply combine hotels, flights and car rentals and we'll reward you with discounts.
If I'm not able to travel, can I cancel my Winchendon travel package?
Because we know life is full of surprises, the answer is yes. To find out more, check out our Customer Service Portal. But generally speaking, if you've booked your package in the last 24 hours, you may be able to cancel or change it with no penalties. Your airline, hotel or car rental company may charge a fee if you made your booking a while ago.
How do I get a cheap travel package to Winchendon?
Booking a hotel and flight together with Expedia won't just save valuable time --- it'll save you a tidy sum too. A Winchendon travel package makes it a breeze to arrange your dream adventure. With more than 550 airlines around the world to select from, finding convenient flights that suit your busy schedule won't be a challenge. In addition to that, we've got over 1,000,000 properties globally to pick from. Now that's what we call choice. No matter who you are, Expedia puts more of the world within your reach.
Does Expedia offer Book Now, Pay Later Winchendon holidays?
Your bank balance shouldn't get in the way of taking a holiday, so Expedia has worked out a solution to help. Now that we've joined forces with online lender Klarna, it's easier than ever to book a fabulous getaway without drying up your savings. Klarna offers flexible payment options at checkout that take the stress out of budgeting for your trip. Consider one of these flexible payment options:

  • Pay monthly holidays: Escape on that dream holiday sooner with Klarna's convenient monthly instalment plans. If paying a little each month sounds right for you, pick this option during the checkout process.
  • Pay in instalments holidays: If you'd like to pay for your escape in multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: Clicking on the "book now" button is much easier with this payment option. Simply put down a small deposit on your booking and then start packing your bags.

What are the top hotels in Winchendon?
Boston Park Plaza and Embassy Suites Boston Logan Airport are two of the most sought-after properties in Winchendon. Why not check out the amenities and rates at each and then decide?
How far in advance should I book my Winchendon holiday?
While not all air carriers release ticket prices early, it's usually possible to compare international flights on Expedia up to 12 months in advance. This is when you'll score some incredible deals. If you're booking last minute, you might get lucky. Low prices occasionally appear a few weeks prior to departure.
What does an Expedia Winchendon travel package include?
From flights and hotels to rental cars, Expedia can help you create a Winchendon package that fits you. Holidaying for a while? Give some thought to a flight, hotel and rental car bundle. If your break is short, a hotel and airfare deal could be what you're after. Experiences can also be added after you've booked. Our travel packages make it easy to plan and save.
What should I know before booking a Winchendon travel package?
When you book your hotels, flights and car rentals together, you'll nab fantastic discounts. Whether you're planning a mountain getaway in a cabin or want to stay in a comfortable hotel in the city, Expedia will make it happen for less.
Can I choose my airline with a Winchendon Expedia travel package?
With a travel package, you're the boss. Whether you want to fly to Winchendon in business or coach, simply select from the available airline options. Expedia has access to more than 550 airline partners all over the world.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.